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Cheap flights from New York to Chicago from $157

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 25/7. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
11 Aug — 18 Aug1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from New York to Chicago are usually found in January or February, booked 83 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from New York to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from New York to Chicago
Explore the most affordable flight options available from New York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 July 2026.

Fri 14/821:45
EWR
-
ORD
Nonstop2h 37m
United Airlines
Tue 18/807:05
ORD
-
EWR
Nonstop2h 17m
United Airlines
Deal found 11/7$298
Tue 4/805:30
EWR
-
ORD
Nonstop2h 45m
American Airlines
Thu 6/820:36
ORD
-
EWR
Nonstop2h 23m
American Airlines
Deal found 11/7$299
Fri 30/1009:40
EWR
-
ORD
1 stop4h 21m
Delta
Sun 1/1106:30
ORD
-
EWR
1 stop5h 27m
Delta
Deal found 10/7$300
Wed 5/820:19
EWR
-
ORD
Nonstop2h 47m
United Airlines
Sun 9/806:00
ORD
-
EWR
Nonstop2h 12m
United Airlines
Deal found 8/7$302
Wed 2/909:15
EWR
-
ORD
Nonstop2h 43m
United Airlines
Fri 4/919:45
ORD
-
EWR
Nonstop2h 22m
United Airlines
Deal found 10/7$305
Thu 6/806:00
EWR
-
ORD
Nonstop2h 42m
United Airlines
Mon 10/821:30
ORD
-
EWR
Nonstop2h 23m
United Airlines
Deal found 9/7$311
Wed 26/821:45
EWR
-
ORD
Nonstop2h 37m
United Airlines
Tue 1/905:00
ORD
-
EWR
Nonstop2h 14m
United Airlines
Deal found 8/7$312
Wed 12/820:29
EWR
-
ORD
Nonstop2h 46m
United Airlines
Sun 16/805:00
ORD
-
EWR
Nonstop2h 14m
United Airlines
Deal found 11/7$313
Fri 25/921:45
EWR
-
ORD
Nonstop2h 36m
United Airlines
Sun 27/907:30
ORD
-
EWR
Nonstop2h 18m
United Airlines
Deal found 7/7$315
Fri 24/716:45
EWR
-
ORD
Nonstop2h 49m
United Airlines
Thu 30/708:40
ORD
-
EWR
Nonstop2h 26m
United Airlines
Deal found 8/7$319

Find flight deals from New York to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from New York (NYC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 12 July 2026.

Round-trip from

$298

One-way from

$157

Popular in

June

Cheapest in

January

Average price

$420
American Airlines
  • American Airlines
  • 2/8-6/8
  • Nonstop
  • 5h 04m total
  • New York to Chicago
Search Deals
United Airlines
  • United Airlines
  • 25/7
  • Nonstop
  • 2h 47m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($102 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average return price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from New York to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 647,157 searches. Data last updated 12 July 2026.
Use the filters below to find and compare flights from New York to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight
Fastest return journey

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 29/12

07:00-08:30

Nonstop2h 30m

Chicago O'Hare Intl

Sun 3/1

06:00-09:06

Nonstop2h 06m

$298

NewarkChicago

EWR - ORD

EWRORD

Newark

Sun 2/8

07:15-09:00

Nonstop2h 45m

Chicago O'Hare Intl

Wed 5/8

21:30-00:53

Nonstop2h 23m

$325

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 21/10

13:00-16:24

1 stop4h 24m

Chicago O'Hare Intl

Sun 25/10

06:30-12:57

1 stop5h 27m

$334

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 28/8

21:45-23:22

Nonstop2h 37m

Chicago O'Hare Intl

Mon 31/8

05:00-08:14

Nonstop2h 14m

$335

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 18/8

20:29-22:15

Nonstop2h 46m

Chicago O'Hare Intl

Wed 19/8

07:05-10:22

Nonstop2h 17m

$342

NewarkChicago

EWR - ORD

EWRORD

Newark

Sun 9/8

07:59-09:43

Nonstop2h 44m

Chicago O'Hare Intl

Sun 9/8

21:30-00:53

Nonstop2h 23m

$361

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 7/8

08:00-09:37

Nonstop2h 37m

Chicago O'Hare Intl

Sat 8/8

06:00-09:12

Nonstop2h 12m

$377

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 29/7

06:00-07:42

Nonstop2h 42m

Chicago O'Hare Intl

Sat 1/8

20:07-23:39

Nonstop2h 32m

$397

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 23/10

21:45-23:21

Nonstop2h 36m

Chicago O'Hare Intl

Tue 27/10

07:00-10:08

Nonstop2h 08m

$413

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 23/10

21:45-23:21

Nonstop2h 36m

Chicago O'Hare Intl

Wed 28/10

06:00-09:06

Nonstop2h 06m

$413

Flights are sorted by cheapest return flights first.

Deals found on 12/7

Showing 1-10 of 24 resultsSorted by cheapest first
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Best time to book a flight from New York to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New York with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago

What is the cheapest month to book a flight from New York to Chicago?

Currently, January is the cheapest month in which you can book a flight from New York to Chicago (average of $285). Flying from New York to Chicago in June is currently the most expensive (average of $503). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from NYC to CHI?

Find hourly flight availability from New York to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 12 July 2026.

When flying from New York to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 83% versus a flight in the afternoon.

Weekly flight availability from New York to Chicago

Explore weekly flight availability from New York to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 12 July 2026.

The most flights from NYC to CHI are scheduled on a Friday (201 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (132 on average).

How much does it cost for a return flight from New York to Chicago?

How often are flights from New York to Chicago delayed?

About 19% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 158 minutes.

What is the most punctual flight time for New York to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on New York to Chicago flights?

Over the past year, United Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.

How far ahead should I book a flight from New York to Chicago?

The best time to book flights from New York to Chicago is 37 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Related info for your journey

Find useful and relevant information for your journey from New York to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from New York to Chicago?

    Airlines like American Airlines, Delta, and United Airlines fly from New York to Chicago in about 2h 45m. The time it takes to get you to your destination can typically vary by up to 1h 36m. New York and Chicago are separated by a distance of 1152 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most reliable airlines from New York to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from New York to Chicago on time: Malaysia Airlines (93%), TAP AIR PORTUGAL (88%), American Airlines (86%).

  • Can I find deals for flights from New York to Chicago that include hotel bookings?

    Yes. In addition to deals on New York to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from New York to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New York to Chicago.

  • Can I find deals for business class flights from New York to Chicago?

    Yes. Cheapflights offers flight deals from New York to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New York to Chicago?

    Currently, January is the cheapest month in which you can book a flight from New York to Chicago (average of $285). Flying from New York to Chicago in June is currently the most expensive (average of $503). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for New York to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Newark to O'Hare Intl flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from New York to Chicago?

Cheapflights makes it easy to find New York to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from New York to Chicago?

Cheapflights helps you find that perfect flight to Chicago from New York by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from New York to Chicago with no change fees?

Yes, we can. To see specific flights from New York to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from New York to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from New York today and book when prices fit your budget.

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